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#$Date: 2024-01-06 11:04:45 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288859 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/28/7062833.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7062833
loop_
_publ_author_name
'Fan, Jie'
'Yan, Qinqin'
'Liu, Huaqing'
'Li, Lijun'
'Liu, Zhong-Quan'
'Li, Zejiang'
_publ_section_title
;
 Photo-promoted cascade cyclization of aryl alkynes: access to
 thiocyanate/trifluoromethylthio-containing quinolino[2,1-b]quinazolinones
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20713
_journal_page_last               20717
_journal_paper_doi               10.1039/D3NJ04433E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C23 H12 Cl N3 O S'
_chemical_formula_weight         413.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-09-04 deposited with the CCDC.	2023-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                95.3900(10)
_cell_angle_beta                 107.9320(10)
_cell_angle_gamma                109.8590(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2573(3)
_cell_length_b                   11.1099(4)
_cell_length_c                   11.4634(4)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      2.75
_cell_volume                     917.59(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            57866
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.620
_diffrn_reflns_theta_min         1.999
_exptl_absorpt_coefficient_mu    0.343
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0725P)²+0.3029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4387
_reflns_number_total             5165
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04433e2.cif
_cod_data_source_block           mo_F3_0m
_cod_depositor_comments          'Adding full bibliography for 7062833.cif.'
_cod_database_code               7062833
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.950
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7167(2) 0.82479(15) 0.60646(14) 0.0342(3) Uani 1 1 d . . . . .
C2 C 0.8809(2) 0.93392(18) 0.63019(18) 0.0449(4) Uani 1 1 d . . . . .
H2 H 0.900403 0.974309 0.565466 0.054 Uiso 1 1 calc R U . . .
C3 C 1.0125(3) 0.9807(2) 0.7496(2) 0.0562(5) Uani 1 1 d . . . . .
H3 H 1.121221 1.052850 0.765394 0.067 Uiso 1 1 calc R U . . .
C4 C 0.9842(3) 0.9207(2) 0.84730(19) 0.0604(6) Uani 1 1 d . . . . .
H4 H 1.075863 0.951715 0.927063 0.073 Uiso 1 1 calc R U . . .
C5 C 0.8229(3) 0.8164(2) 0.82697(17) 0.0509(4) Uani 1 1 d . . . . .
H5 H 0.803301 0.778472 0.892938 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6871(2) 0.76749(16) 0.70496(14) 0.0373(3) Uani 1 1 d . . . . .
C7 C 0.5139(2) 0.65951(17) 0.68265(14) 0.0393(3) Uani 1 1 d . . . . .
C8 C 0.2392(2) 0.48482(14) 0.51742(13) 0.0298(3) Uani 1 1 d . . . . .
C9 C 0.2058(2) 0.40357(16) 0.60093(15) 0.0388(3) Uani 1 1 d . . . . .
H9 H 0.292333 0.425405 0.682068 0.047 Uiso 1 1 calc R U . . .
C10 C 0.0465(3) 0.29162(17) 0.56459(17) 0.0420(4) Uani 1 1 d . . . . .
H10 H 0.026466 0.238444 0.620945 0.050 Uiso 1 1 calc R U . . .
C11 C -0.0827(2) 0.25875(15) 0.44484(17) 0.0380(3) Uani 1 1 d . . . . .
C12 C -0.0515(2) 0.33342(15) 0.35901(15) 0.0364(3) Uani 1 1 d . . . . .
H12 H -0.138700 0.309017 0.277849 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1102(2) 0.44576(14) 0.39292(13) 0.0306(3) Uani 1 1 d . . . . .
C14 C 0.1509(2) 0.52202(15) 0.30246(13) 0.0325(3) Uani 1 1 d . . . . .
C15 C 0.3097(2) 0.62824(15) 0.33262(13) 0.0314(3) Uani 1 1 d . . . . .
C16 C 0.44124(19) 0.67399(14) 0.46237(12) 0.0291(3) Uani 1 1 d . . . . .
C17 C 0.3578(2) 0.70398(16) 0.23930(13) 0.0360(3) Uani 1 1 d . . . . .
C18 C 0.3393(3) 0.82330(19) 0.23606(18) 0.0497(4) Uani 1 1 d . . . . .
H18 H 0.303789 0.859229 0.295733 0.060 Uiso 1 1 calc R U . . .
C19 C 0.3739(4) 0.8890(2) 0.1435(2) 0.0651(6) Uani 1 1 d . . . . .
H19 H 0.358810 0.968014 0.140144 0.078 Uiso 1 1 calc R U . . .
C20 C 0.4306(3) 0.8374(2) 0.0567(2) 0.0662(7) Uani 1 1 d . . . . .
H20 H 0.453880 0.881790 -0.004974 0.079 Uiso 1 1 calc R U . . .
C21 C 0.4527(3) 0.7210(3) 0.06081(17) 0.0592(6) Uani 1 1 d . . . . .
H21 H 0.493121 0.687460 0.002939 0.071 Uiso 1 1 calc R U . . .
C22 C 0.4148(2) 0.6526(2) 0.15149(15) 0.0451(4) Uani 1 1 d . . . . .
H22 H 0.427644 0.572779 0.153162 0.054 Uiso 1 1 calc R U . . .
C23 C -0.0864(3) 0.5841(2) 0.12896(16) 0.0524(5) Uani 1 1 d . . . . .
Cl1 Cl -0.28531(6) 0.12050(4) 0.40035(5) 0.05431(15) Uani 1 1 d . . . . .
N1 N 0.58781(18) 0.77826(13) 0.48566(12) 0.0342(3) Uani 1 1 d . . . . .
N2 N 0.39983(17) 0.60355(12) 0.55287(11) 0.0300(2) Uani 1 1 d . . . . .
N3 N -0.1464(4) 0.6629(3) 0.1091(2) 0.0837(7) Uani 1 1 d . . . . .
O1 O 0.4659(2) 0.61920(16) 0.76677(12) 0.0649(4) Uani 1 1 d . . . . .
S1 S -0.01149(6) 0.46175(5) 0.14393(4) 0.04817(15) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 121.71(14) . . ?
N1 C1 C2 118.74(15) . . ?
C6 C1 C2 119.55(14) . . ?
C3 C2 C1 119.68(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.51(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.74(17) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.25(19) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.22(16) . . ?
C1 C6 C7 119.88(13) . . ?
C5 C6 C7 119.88(16) . . ?
O1 C7 N2 121.75(16) . . ?
O1 C7 C6 123.32(15) . . ?
N2 C7 C6 114.93(13) . . ?
C9 C8 C13 118.29(14) . . ?
C9 C8 N2 122.56(13) . . ?
C13 C8 N2 119.14(12) . . ?
C10 C9 C8 120.99(15) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.93(15) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.67(15) . . ?
C12 C11 Cl1 119.34(13) . . ?
C10 C11 Cl1 119.98(13) . . ?
C11 C12 C13 120.38(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.57(13) . . ?
C12 C13 C14 121.43(13) . . ?
C8 C13 C14 118.99(13) . . ?
C15 C14 C13 122.16(13) . . ?
C15 C14 S1 120.86(11) . . ?
C13 C14 S1 116.80(11) . . ?
C14 C15 C16 119.71(13) . . ?
C14 C15 C17 122.86(13) . . ?
C16 C15 C17 117.42(13) . . ?
N1 C16 N2 124.71(12) . . ?
N1 C16 C15 116.61(12) . . ?
N2 C16 C15 118.67(13) . . ?
C18 C17 C22 119.58(16) . . ?
C18 C17 C15 120.57(15) . . ?
C22 C17 C15 119.80(15) . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.30(18) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 119.87(19) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
N3 C23 S1 174.7(2) . . ?
C16 N1 C1 118.80(13) . . ?
C16 N2 C8 120.94(11) . . ?
C16 N2 C7 118.39(12) . . ?
C8 N2 C7 120.46(12) . . ?
C23 S1 C14 99.86(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3791(19) . ?
C1 C6 1.393(2) . ?
C1 C2 1.406(2) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(2) . ?
C7 O1 1.218(2) . ?
C7 N2 1.4326(18) . ?
C8 C9 1.401(2) . ?
C8 C13 1.4118(19) . ?
C8 N2 1.4293(19) . ?
C9 C10 1.380(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(2) . ?
C11 Cl1 1.7321(17) . ?
C12 C13 1.396(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.446(2) . ?
C14 C15 1.351(2) . ?
C14 S1 1.7916(14) . ?
C15 C16 1.4623(18) . ?
C15 C17 1.488(2) . ?
C16 N1 1.2916(19) . ?
C16 N2 1.4124(18) . ?
C17 C18 1.388(3) . ?
C17 C22 1.388(2) . ?
C18 C19 1.389(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 N3 1.152(3) . ?
C23 S1 1.676(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.02(16) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
N1 C1 C6 C5 179.13(15) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
N1 C1 C6 C7 -2.6(2) . . . . ?
C2 C1 C6 C7 176.61(15) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 -178.43(17) . . . . ?
C1 C6 C7 O1 -167.41(18) . . . . ?
C5 C6 C7 O1 10.9(3) . . . . ?
C1 C6 C7 N2 11.8(2) . . . . ?
C5 C6 C7 N2 -169.95(15) . . . . ?
C13 C8 C9 C10 -3.2(2) . . . . ?
N2 C8 C9 C10 178.04(14) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 2.7(3) . . . . ?
C9 C10 C11 Cl1 -178.40(13) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
Cl1 C11 C12 C13 179.59(11) . . . . ?
C11 C12 C13 C8 -2.1(2) . . . . ?
C11 C12 C13 C14 176.61(14) . . . . ?
C9 C8 C13 C12 4.4(2) . . . . ?
N2 C8 C13 C12 -176.85(13) . . . . ?
C9 C8 C13 C14 -174.38(13) . . . . ?
N2 C8 C13 C14 4.4(2) . . . . ?
C12 C13 C14 C15 -177.62(14) . . . . ?
C8 C13 C14 C15 1.1(2) . . . . ?
C12 C13 C14 S1 -2.42(19) . . . . ?
C8 C13 C14 S1 176.31(11) . . . . ?
C13 C14 C15 C16 -4.0(2) . . . . ?
S1 C14 C15 C16 -178.96(11) . . . . ?
C13 C14 C15 C17 176.98(14) . . . . ?
S1 C14 C15 C17 2.0(2) . . . . ?
C14 C15 C16 N1 -178.06(14) . . . . ?
C17 C15 C16 N1 1.1(2) . . . . ?
C14 C15 C16 N2 1.3(2) . . . . ?
C17 C15 C16 N2 -179.61(13) . . . . ?
C14 C15 C17 C18 102.66(19) . . . . ?
C16 C15 C17 C18 -76.42(19) . . . . ?
C14 C15 C17 C22 -74.8(2) . . . . ?
C16 C15 C17 C22 106.09(17) . . . . ?
C22 C17 C18 C19 1.4(3) . . . . ?
C15 C17 C18 C19 -176.08(17) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C18 C17 C22 C21 -0.1(3) . . . . ?
C15 C17 C22 C21 177.42(15) . . . . ?
C20 C21 C22 C17 -1.2(3) . . . . ?
N2 C16 N1 C1 1.2(2) . . . . ?
C15 C16 N1 C1 -179.55(12) . . . . ?
C6 C1 N1 C16 -4.3(2) . . . . ?
C2 C1 N1 C16 176.50(14) . . . . ?
N1 C16 N2 C8 -176.47(13) . . . . ?
C15 C16 N2 C8 4.3(2) . . . . ?
N1 C16 N2 C7 8.7(2) . . . . ?
C15 C16 N2 C7 -170.54(13) . . . . ?
C9 C8 N2 C16 171.64(13) . . . . ?
C13 C8 N2 C16 -7.1(2) . . . . ?
C9 C8 N2 C7 -13.7(2) . . . . ?
C13 C8 N2 C7 167.62(13) . . . . ?
O1 C7 N2 C16 164.71(17) . . . . ?
C6 C7 N2 C16 -14.5(2) . . . . ?
O1 C7 N2 C8 -10.1(2) . . . . ?
C6 C7 N2 C8 170.67(13) . . . . ?
C15 C14 S1 C23 -69.06(15) . . . . ?
C13 C14 S1 C23 115.68(13) . . . . ?
